2-Propanol, reaction products with ammonia, distn. residues → 5-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine hydrate

Participants

Reaction Conditions

Reaction Steps

A mixture of intermediate 26 (0.0083 mol) in THF (80 ml) was cooled to 5° C. under N2 flow. NH3/iPrOH (80 ml) was added dropwise. The mixture was stirred at 5° C. for 1 hours, then brought to room temperature. The mixture was stirred at room temperature overnight, poured out into ice water and extracted with DCM. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH 96/4/0.2). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 1.37 g (33%) of 5-(3-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-α-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine hydrate (1:1) (intermediate 27), mp. 150° C.

Provenance & Evidence